Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles

• Published in: Carbohydrate research Vol. 337; no. 24; pp. 2419 - 2425
• Main Authors: Fascio, Mirta L, Alvarez-Larena, Angel, D'Accorso, Norma B
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 29.11.2002; Elsevier
• Subjects: Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Crystallography, X-Ray; Heterocyclic Compounds, 4 or More Rings - chemical synthesis; Heterocyclic Compounds, 4 or More Rings - chemistry; Intramolecular 1,3-dipolar cycloaddition; Isoxazoles - chemical synthesis; Isoxazoles - chemistry; Isoxazolines; Life Sciences & Biomedicine; Nuclear Magnetic Resonance, Biomolecular; Physical Sciences; Science & Technology; Stereocontrol, NMR spectroscopy; Stereoisomerism; X-Ray crystallography; Intramolecular 1,3-dipolar cycloaddition; Isoxazolines; X-Ray crystallography; Stereocontrol, NMR spectroscopy; isoxazolines; X-ray crystallography; stereocontrol, NMR spectroscopy; NITRILE OXIDE CYCLOADDITION; intramolecular 1,3-dipolar cycloaddition
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(02)00258-6

Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution 1H and 13C NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. Graphic